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129.6, 128.0, 127.7, 125.7, 121.1, 21.4, 21.3; HRMS (m/z) [M 142 °C); Rf = 0.47 (EtOAc:PE = 25:75); H NMR (400 MHz,
+ H]+ calcd for C16H15N2O 251.1179, found 251.1185.
CDCl3) δ 8.34-8.28 (m, 1H), 7.79-7.70 (DmO,I:21H0.)1,0379./5C45R(Ad1t1,262A
6-methyl-2-propylquinazolin-4(3H)-one (1q). Yield: 100 mg, 9.6, 2.8 Hz, 2H), 7.51-7.47 (m, 1H), 7.04 (dt, = 9.6, 2.8 Hz,
99%; white solid, mp 244-246 °C (lit.19 mp 244.3-244.8 °C); Rf 2H), 3.88 (s, 3H), 3.54 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
J =
J
= 0.30 (EA/PE 25:75); 1H NMR (400 MHz, DMSO-
(br, s, 1H), 7.88 (s, 1H), 7.59 (d, = 8.0 Hz, 1H), 7.50 (d,
8.4 Hz, 1H), 2.57 (t, = 7.6 Hz, 2H), 2.43 (s, 3H), 1.74 (sext,
= 7.6 Hz, 2H), 0.94 (t,
DMSO- 6) δ 162.2, 156.8, 147.4, 136.0, 135.9, 127.1, 125.5, Yield: 112 mg, 83%; white solid, mp 166-168 °C; Rf = 0.25
121.0, 36.7, 21.2, 20.7, 14.0; HRMS (m/z) [M + H]+ calcd for (EtOAc:PE = 16:84); 1H NMR (400 MHz, CDCl3) δ 8.32 (dd,
d6) δ 12.09 162.9, 160.9, 156.0, 147.4, 134.2, 129.7, 127.7, 127.4, 126.8,
J
J
=
J
126.6, 120.3, 114.2, 55.5, 34.5; HRMS (m/z) [M + H]+ calcd
for C16H15N2O2 267.1128, found 267.1124.
J
J
= 7.6 Hz, 3H); 13C NMR (100 MHz, 2-(4-Chlorophenyl)-3-methylquinazolin-4(3H)-one
(
1x).21
d
J
C12H15N2O 203.1179, found 203.1179.
= 8.0, 0.8 Hz, 1H), 7.79-7.71 (m, 2H), 7.56-7.48 (m, 5H), 3.50
6-Chloro-2-(p-tolyl)quinazolin-4(3H)-one (1r). Yield: 103 mg, (s, 3H); 13C NMR (100 MHz, CDCl3) δ 162.6, 155.0, 147.1,
76%; white solid, mp > 300 °C (lit.11 mp > 300 °C); Rf = 0.30 136.3, 134.4, 133.7, 129.5, 129.1, 127.5, 127.2, 126.7, 120.5,
1
(EtOAc:PE = 25:75); H NMR (400 MHz, DMSO-
d
6) δ 12.65 34.2; HRMS (m/z) [M + H]+ calcd for C15H12ClN2O 271.0633,
(br, s, 1H), 8.10-8.08 (m, 3H), 7.86 (dd,
7.75 (d, = 8.8 Hz, 1H), 7.37 (d, = 8.0 Hz, 2H), 2.40 (s, 3H); 4-(3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)benzonitrile (1y).
13C NMR (100 MHz, DMSO-
6) δ 161.8, 153.2, 148.1, 142.2, Yield: 86 mg, 66%; white solid, mp 216-218 °C; Rf = 0.40
135.2, 131.0, 130.14, 130.08, 129.7, 128.2, 125.3, 122.6, 21.5; (EtOAc:PE = 25:75); 1H NMR (400 MHz, CDCl3) δ 8.34 (dd,
HRMS (m/z) [M + H]+ calcd for C15H12ClN2O 271.0633, found = 8.0, 1.2 Hz, 1H), 7.88-7.82 (m, 2H), 7.82-7.76 (m, 1H), 7.76-
271.0637.
7.69 (m, 3H), 7.58-7.52 (m, 1H), 3.49 (s, 3H); 13C NMR (100
J = 8.4, 2.4 Hz, 1H), found 271.0632.
J
J
d
J
6-Chloro-2-propylquinazolin-4(3H)-one (1s). Yield: 100 mg, MHz, CDCl3) δ 162.3, 154.1, 147.0, 139.4, 134.6, 132.7, 129.0,
90%; white solid, mp 246-248 °C (lit.20 mp 248-250 °C); Rf
=
127.62, 127.56, 126.8, 120.6, 117.9, 114.0, 34.1; HRMS (m/z)
6) δ [M + Na]+ calcd for C16H11N3ONa 284.0794, found 284.0791.
= 8.8, 2.0 3-Methyl-2-(4-nitrophenyl)quinazolin-4(3H)-one (1z). Yield: 87
J = 7.6 Hz, 2H), 1.74 mg, 62%; white solid, mp 191-192 °C; Rf = 0.30 (EtOAc:PE =
1
0.40 (EtOAc:PE = 25:75); H NMR (400 MHz, DMSO-
d
12.35 (br, s, 1H), 8.01 (d,
Hz, 1H), 7.62 (d, = 8.8 Hz, 1H), 2.58 (t,
(sext, = 7.6 Hz, 2H), 0.94 (t,
= 7.6 Hz, 3H); 13C NMR (100 25:75); H NMR (400 MHz, CDCl3) δ 8.43-8.40 (m, 2H), 8.35
MHz, DMSO- 6) δ 161.2, 158.4, 148.1, 134.8, 130.5, 129.5, (dd, = 8.0, 0.8 Hz, 1H), 7.82-7.78 (m, 3H), 7.74-7.72 (m, 1H),
125.1, 122.5, 36.8, 20.5, 13.9; HRMS (m/z) [M + H]+ calcd for 7.58-7.54 (m, 1H), 3.50 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
J = 2.0 Hz, 1H), 7.79 (dd, J
J
1
J
J
d
J
C11H12ClN2O 223.0633, found 223.0647.
162.2, 153.8, 148.6, 146.9, 141.1, 134.6, 129.4, 127.7, 127.6,
6-Nitro-2-propylquinazolin-4(3H)-one (1t). Yield: 114 mg, 126.8, 124.1, 120.6, 34.1; HRMS (m/z) [M + Na]+ calcd for
98%; light yellow solid, mp 264-266 °C (lit.20 mp 264-266 °C); C15H11N3O3Na 304.0693, found 304.0687.
R
f = 0.20 (EtOAc:PE = 25:75); 1H NMR (400 MHz, DMSO-d6
)
3-Methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one
1aa). Yield: 108 mg, 71%; white solid, mp 126-127 °C; Rf =
δ 12.66 (br, s, 1H), 8.77 (d,
2.8 Hz, 1H), 7.78 (d, = 9.2 Hz, 1H), 2.64 (t,
1.77 (sext, = 7.6 Hz, 2H), 0.95 (t,
= 7.2 Hz, 3H); 13C NMR (dd,
(100 MHz, DMSO- 6) δ 161.9, 161.5, 153.6, 144.8, 129.0, 7.73 (m, 1H), 7.69 (t,
128.7, 122.3, 121.2, 37.0, 20.5, 13.9; HRMS (m/z) [M + H]+ (s, 3H); 13C NMR (100 MHz, CDCl3) δ 162.4, 154.5, 147.0,
calcd for C11H12N3O3 234.0873, found 234.0874. 136.1, 134.5, 131.5 (q, JC-F = 32.8 Hz), 131.4, 129.5, 127.5,
3-Methoxy-2-(p-tolyl)quinazolin-4(3H)-one (1u). Yield: 81 mg, 127.4, 126.8 (q, JC-F = 3.7 Hz), 126.7, 125.2 (q, C-F = 3.9 Hz),
61%; white solid, mp 157-158 °C; Rf = 0.30 (EtOAc:PE = 123.5 (d,
C-F = 271.1 Hz), 120.6, 34.2; HRMS (m/z) [M + Na]+
16:84); 1H NMR (400 MHz, CDCl3) δ 8.33 (dt,
= 8.0, 0.8 Hz, calcd for C16H11F3N2ONa 327.0716, found 327.0706.
1H), 7.84-7.81 (m, 2H), 7.78-7.76 (m, 2H), 7.53-7.47 (m, 1H), 3-Butyl-2-(p-tolyl)quinazolin-4(3H)-one (1ab). Yield: 110 mg,
7.32 (d, f = 0.45 (EtOAc:PE = 16:84);
= 8.0 Hz, 2H), 3.77 (s, 3H), 2.45 (s, 3H); 13C NMR 75%; white solid, mp 78-79 °C;
(100 MHz, CDCl3) δ 158.1, 153.2, 146.6, 141.2, 134.4, 129.4, 1H NMR (400 MHz, CDCl3) δ 8.37-8.28 (m, 1H), 7.79-7.69 (m,
129.1, 129.0, 127.9, 126.8, 126.7, 122.5, 63.9, 21.5; HRMS 2H), 7.53-7.45 (m, 1H), 7.45-7.38 (m, 2H), 7.31 (d, = 8.0 Hz,
= 8.0 Hz, 2H), 2.44 (s, 3H), 1.64-1.54 (m, 2H),
J
= 2.8 Hz, 1H), 8.50 (dd,
= 7.2 Hz, 2H), 0.25 (EtOAc:PE = 16:84); H NMR (400 MHz, CDCl3) δ 8.34
= 8.0, 0.8 Hz, 1H), 7.89 (s, 1H), 7.82-7.77 (m, 3H), 7.75-
= 7.6 Hz, 1H), 7.56-7.52 (m, 1H), 3.50
J
= 8.8,
(
1
J
J
J
J
J
d
J
J
J
J
J
R
J
(m/z) [M + Na]+ calcd for C16H14N2O2Na 289.0947, found 2H), 4.00 (t,
289.0933. 1.18 (sext,
J
J
= 7.6 Hz, 2H), 0.78 (t,
J
= 7.2 Hz, 3H); 13C NMR
3-Methyl-2-(p-tolyl)quinazolin-4(3H)-one (1v). Yield: 116 mg, (100 MHz, CDCl3) δ 162.2, 156.4, 147.2, 139.8, 134.2, 132.7,
93%; white solid, mp 137-139 °C (lit.21 mp 138 °C);Rf = 0.30 129.3, 127.7, 127.4, 126.8, 126.7, 120.8, 45.7, 30.7, 21.4, 19.9,
1
(EtOAc:PE = 16:84); H NMR (400 MHz, CDCl3) δ 8.34-8.30 13.4; HRMS (m/z) [M + H]+ calcd for C19H21N2O 293.1648,
(m, 1H), 7.78-7.68 (m, 2H), 7.53-7.41 (m, 3H), 7.32 (d,
J = 8.0 found 293.1648.
Hz, 2H), 3.50 (s, 3H), 2.43 (s, 3H); 13C NMR (100 MHz, 3-Phenyl-2-(p-tolyl)quinazolin-4(3H)-one (1ac). Yield: 102 mg,
CDCl3) δ 162.8, 156.2, 147.3, 140.2, 134.2, 132.5, 129.4, 127.9, 65%; white solid, mp 174-176 °C (lit.22 mp 178 °C); Rf = 0.25
127.4, 126.8, 126.6, 120.4, 34.3, 21.4; HRMS (m/z) [M + H]+ (EtOAc:PE = 16:84); H NMR (400 MHz, CDCl3) δ 8.35 (d,
1
J
calcd for C16H15N2O 251.1179, found 251.1179.
2-(4-Methoxyphenyl)-3-methylquinazolin-4(3H)-one
Yield: 107 mg, 80%; white solid, mp 142-143 °C (lit.21 mp = 8.0 Hz, 2H), 2.26 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
= 8.0 Hz, 1H), 7.83-7.77 (m, 2H), 7.54-7.50 (m, 1H), 7.35-7.28
1w). (m, 3H), 7.22 (d, = 8.0 Hz, 2H), 7.17-7.15 (m, 2H), 7.01 (d, J
(
J
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